Formal charges have their plusses and minuses. Har har.
One one hand, they're an indispensable accounting tool. If a molecule bears a charge, it would drive us nuts (for nomenclature reasons) if we didn't adopt some kind of system where a charge was unambiguously assigned to one atom.
In many … [Read more...]

When learning any new reaction, I think you always have to start with the "what". What bonds are forming, and what bonds are breaking.
After you answer "what", then you can start asking "where" - as in , "where are the electrons of the reactants?" What areas are electron rich? What areas are … [Read more...]

If you think of electrons as the currency of chemistry, reactions are transactions of electrons between atoms. Just like double entry book keeping was developed to formalize how financial transactions are recorded, chemists have developed their own convention for showing transactions of electrons … [Read more...]

The most important question when learning a new reaction is recognizing "What Bonds Form, What Bonds Break?"
If that's #1, then what's the second most important question to ask yourself?
I think it is: "how do the electrons move?"
[I have a friendly disagreement with a lot of instructors … [Read more...]

The four posts on acid-base, substitution, addition, and elimination covered the 4 main reactions in organic chemistry I. In this second series of posts we go beyond these to introduce a few of the less common (but still important) reactions you learn in organic chemistry 1. We've talked … [Read more...]

The four posts on acid-base, substitution, addition, and elimination covered the 4 main reactions in organic chemistry I. In this second series of posts we go beyond these to introduce a few of the less common (but still important) reactions you learn in organic chemistry 1. We talked about … [Read more...]

As part 4 of the most important reactions you learn in org 1, (acid-base, substitution, and addition) here's an introduction to the elimination reaction. This series requires that you understand how to read line diagrams (click for video introduction) as well as to understand what wedge-dash … [Read more...]

A few months ago after putting up this post on "Hidden Hydrogens, Hidden Lone Pairs, and Hidden Counterions", commenter Stewie Griffin made me aware of this little gem:
With regards to hidden hydrogens, don’t forget “Grossman’s Rule” (named by Robert Grossman in his “Art of Writing Reasonable … [Read more...]

Following up on the 4 most important reactions you learn in Org 1, and the posts on acid-base and substitution reactions, here's the third in the series: addition reactions.
You'll have to know line diagrams to get this - see the video here - and to truly grok the point of the last two images, … [Read more...]

Last week Diana left this comment:
I recently had my first orgo exam and one of the concepts that I have trouble visceralizing is Hammond's Postulate. I can follow the explanation in my textbook (L.G. Wade, Jr. 7th edition), but I don't really grasp it. Is there an alternative intuitive … [Read more...]